Lithium Hydroxide → (+/-)-trans-2-(4-Chlorophenyl)-4-oxocyclohexanecarboxylic acid

HRID 1743939

Reaction equation

HRID 1743939 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][C:12](=[O:14])[CH2:11][CH2:10][C@H:9]2[C:15]([O:17]C)=[O:16])=[CH:4][CH:3]=1.[OH-].[Li+].Cl.[Cl-].[Na+].O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:13][C:12](=[O:14])[CH2:11][CH2:10][C@H:9]2[C:15]([OH:17])=[O:16])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 68516321Methyl trans-2-(4-chlorophenyl)-4-oxocyclohexanecarboxylateHCID 131718760Hydrochloric acid brine

Product 1

HCID 21017822(+/-)-trans-2-(4-Chlorophenyl)-4-oxocyclohexanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of methyl trans-2-(4-chlorophenyl)-4-oxocyclohexanecarboxylate (1.05 g, 3.94 mmol) and 1 N lithium hydroxide (5.91 mL, 5.91 mmol) in tetrahydrofuran (5 mL) was heated at reflux for approximately 1 h. After cooling to room temperature, the reaction mixture was poured into 1 N hydrochloric acid/brine (1:1) and extracted three times with methylene chloride. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude title compound was used without further purification in the subsequent reaction.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately 1 h
  3. extractionextracted three times with methylene chloride
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude title compound was used without further purification in the subsequent reaction

Sources & evidence

ORD record
ord-2a81883c8cc6425c9b1f364cc91d3167
Source dataset
uspto-grants-2006_03
Patent number
US07012084B2

Linked notes

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